FANTASIES FULLFILLED
Chapter 1
First Time for Diana
Trembling with the erotic mixture of fear and excitement Darrell rang the
doorbell. Under his office regulation 3 piece suit and white shirt, his
female alter ego, Diana, was dressed in her most seductive black lingerie
- padded bra, garter belt, nylons, and her most exquisite silk panties
which cocooned Darrell's hot throbbing hardness. His briefcase held his
long lycra evening gloves and silicon breasts, along with the silk scarf
he had been instructed to bring.
It was THAT TIME for Diana and she had insisted on Darrell wearing a
maternity size sanitary pad "for that extra protection" as the adverts
had it. All day at the office Darrell had been sitting on the pad,
alternately tensing and relaxing his sissyboy vaginal muscles, and as he
stood on the doorstep he could feel the pad had worked itself into his
little pink rosebud.
Even worse he had abstained from masturbating all day to allow the cum to
build up in his balls. Darrell was a compulsive masturbator, continually
fondling his cock and balls in their pantied cocoon, behind the security
of his office desk, Frequently he visited the washroom to masturbate
whenever the excitement became too much to bear. Since his first
masturbatory experience as a young man wearing Mummy's silky directoire
knickers, Darrell could not remember abstaining for so long a period. Now
his cock cried out for masturbatory relief.
As he rang the doorbell again Darrell felt the inner turmoil of dread and
desire welling up inside him. This was the first time he had shared his
secret passions with anyone other than Diana. Now the timorous Darrell
wanted to flee the scene while the ever adventurous Diana yearned to
press ahead to savour further erotic excitements.
It had all seemed so simple at the start:
"Calling all sissyboys. Let Mistress Natasha help you to realise your
wildest dreams. All fantasies and fetishes considered. First timers most
welcome, please ask Mistress Natasha for her special introductory
service."
And that voice when Darrell rang the number printed on the card and
described his lifelong infatuation with soft silky lingerie and all
things feminine. It's sexiness sent the most wonderful erotic shivers
down his spine, and got his cock at its most throbbing hardness.
"I simply adore lingerie loving sissyboys, daahling," cooed the soft
seductive voice, "Almost all of my clients wear their panties 24/7 as you
do, and a lot wear more than panties under their business suits. And that
is only the beginning. You should see how some of my clients satisfy
their love of soft silky lingerie. A whole new world of sissyboy erotic
delights awaits you."
As Darrell listened to that voice his hand fondled his hardness through
his silky panties, and he fantasised about what she was wearing and if
she was also pleasuring herself. By the erotic tone of her voice and the
way she occasionally gasped, Darrell was almost positive she was playing
with her pussyhole.
After Darrell had described his innermost secret fantasy, the voice
answered "I haven't come across that particular fantasy before, but now I
think of it, it all sounds so obvious and simple. At our first meeting
we'll discuss how, together, we can make it come true. But first you
simply must try my special introductory service, you'll find the
experience most erotic."
The click from the door brought Darrell out of his reverie. Somewhere
inside the house an unseen hand had pressed an electronic switch to
unlock the door. It was now or never - to turn and flee or to enter and
experience new erotic adventures. As usual it was Diana who took control
of the situation.
Pushing open the door, Darrell entered a hallway lit by subdued lighting.
A blow-up doll saucily dressed in a French maid's short black uniform
trimmed with white piping at the edges, gestured towards an open door at
the end of the hallway. Peering through the gloom Darrell could see that
the room was bathed in a soft orange-red glow.
As Darrell heard the click of the street door shutting behind him, he
slowly walked towards the open door. Drawing closer he saw a black silk
Grecian style nightdress draped across a chair, forming a backdrop to the
upright riding crop which leaned against it. With each step Darrell felt
the erotic excitement welling inside him. His cock throbbed in the silken
cocoon of his panties. What else lay behind the door? Darrell was out of
his depth and wondered whether to continue, forgetting that behind him
the locked outer door blocked his only means of escape. He could only go
forward.
An invisible magnet seemed to draw him ever closer towards the open door.
Now he stood on the threshold wondering whether or not to enter the room.
As usual Diana took control, and forced him to enter the room.
Blinking his eyes in the light he saw in the far corner a lady he took to
be Mistress Natasha. And what a lady. Dressed all in black she wore a
tight bustier which sat just above her hips emphasising her slim waist,
her legs encased in black stockings which to Darrell's trained eye were a
mixture of lycra and nylon, her feet shod in 4 inch stiletto heels, a
tight pearl choker encircled her swanlike neck, and her arms were encased
in long evening gloves which reached almost to her shoulders. Her long
auburn hair framed her beautiful face. The black of her attire
contrasting erratically with the smooth milky whiteness of her skin.
But what astonished Darrell most of all was what emerged from her crotch.
Mistress was fondling the most realistic dildo Darrell had ever seen.
Even Darrell, who had seen and fondled many cocks in his years of
dalliance with other sissyboys in gay venues, was awed by the spectacle.
Mistress Natasha, for it was she, smiled sweetly at his wonderment.
"Are you dressed underneath like a good sissyboy, Darrell?" she asked. as
she played with herself.
Darrell could only nod in reply and then stammered, "Actually, I'm Diana,
Mistress."
"Until you have completely shed your male clothes and wear only feminine
finery, you will be Darrell." She pointed to a screen in the opposite
corner. "Now go behind that screen and don't let me see you until you
have discarded every vestige of your male persona."
Darrell walked behind the screen and trembling with a mixture of erotic
excitement and fear, removed his shoes and three piece suit, finally
discarding his shirt. As he divested himself of his male clothes he could
feel the throbbing hardness between his legs, and he gently fondled his
silken encased cock and knob. The silicon breasts and evening gloves
completed his ensemble. Now Darrell was transformed into his female
persona as Diana. He even felt like a woman. Not knowing what to do with
his silk scarf he draped it around his neck. With his gloved hands he
fondled his throbbing cock through his silky panties one last time. Now
he really was Diana not Darrell.
In reality Darrell consisted of three people, so the marriage was rather
crowded as someone once remarked. There was Darrell, a gay, effeminate,
lingerie loving sissyboy who whiled away his days of boredom in the
office fondling his throbbing cock in its silken cocoon. At night he
trawled through gay bars and saunas in the never ending search for
pretty, effeminate young men like himself, for a few brief passionate
moments of kissing and mutual fondling. Diana, his lesbian alter ego who
ruled the household taking all the decisions affecting him. And then
there was Miss Dianella, as he liked to call the young lady who hung
between his legs. All three lived in a menage a trois, wrapped up in the
same body that presented itself to the world as Darrell.
All his life Darrell had loved the erotic sensations that came from the
touch of soft silky lingerie. Mummy had always wanted a little girl and
loved to dress him in girls' clothes, and in Darrell she actually had a
little girl, albeit one with a cock between her legs.. Even as a small
child he had worn Mummy's silky directoire knickers under his male
clothes, even sleeping in these knickers at night. As Darrell grew older
he had gradually amassed a large collection of Mummy's discarded
lingerie, and, by the time he had graduated from high school to go to
university, he was wearing Mummy's directoire knickers 24/7, as well as
much of her other lingerie whenever he could. At university he had
encountered many sissyboys who shared his erotic passions and through
them he had expanded his sexual repertoire.
Diana had always been a part of Darrell's life. Initially she was a shy
girl who had stayed in the background, but as Darrell grew older she
gradually came to the fore and now Darrell retreated into his female
persona as Diana at every opportunity. Even when Diana was having her
periods she made Darrell wear a thick sanitary pad pushed up into his
little pink rosebud. Not that Darrell objected, he savoured the
experience of feeling more girlie, and coming ever closer to the
femininity he craved.
It was Diana who chose his lingerie for him when they shopped, and each
morning she selected what she wanted him to wear under his male clothes
for the day. After all she wanted to pleasure herself too. Diana had such
exquisite taste in lingerie as did Mummy, and Darrell was content for her
to take charge of his wardrobe. Thanks to Diana he now had a most
wonderful collection of lingerie which would be the envy of many a real
girl.
And both Darrell and Diana passionately loved Miss Dianella, lavishing
every care and attention on her, and making sure that the young lady was
perpetually cocooned in the finest silky panties Diana could find. In
return the young lady showed her appreciation by giving them both many
hours of erotic pleasure.
Both Darrell and Diana were dedicated slaves to the erotic passions that
can only come from the silkiness of directoire knickers, and loved
wearing these most erotic garments. As he sat clad in his directoire
knickers gazing lovingly and the naked bodies of beautiful young men in
his large collection of homo-erotica, he would caress and fondle Miss
Dianella through the silkiness of his knickers, until he reached such a
state of excitement that he just had to masturbate to relieve the tension
that had built up inside him.
While Darrell loved to fondle and masturbate Miss Dianella with his right
hand. Diana preferred to fondle and masturbate the young lady with her
left hand as she sat in her silky knickers leafing through lingerie
catalogues selecting silky delicacies for Darrell, or reading her
collection of lesbian erotica. Darrell loved when Diana took control of
Miss Dianella and masturbated the young lady, relishing the completely
different erotic experience.
"Are you ready yet?"
Again Darrell was recalled from his reverie.
"Yes Mistress."
"Then show yourself in all your feminine glory."
Darrell slowly emerged from behind the screen and stood before Mistress
Natasha resplendent in his black lingerie.
Feeling very nervous, Darrell slowly edged round the screen into the full
view of Mistress Natasha.
"My, these are pretty panties, Diana. Do you select all Darrell's
lingerie for him?"
"Yes, Mistress," was all Darrell could reply he was so overwhelmed by the
erotic pleasure of the occasion.
Darrell was used to being complimented on his lingerie. Not that he
deserved it, as it was Diana who always made the selection. When shopping
for lingerie the salesladies had often complimented Darrell on his
exquisite taste in silky lingerie, telling him that he was such a delight
to serve. Darrell accepted the compliments on behalf of Diana, while deep
down between his legs he could feel Miss Dianella's excitement as she
hardened in her silken cocoon.
Mistress Natasha walked over to the chair and took up her riding crop.
For a moment Darrell feared that she was going to strike him. Instead
Mistress slowly encircled him, riding crop in one hand while the other
fondled her dildo. Several times Darrell could sense Mistress feeling the
tightness of his bra strap and adjusting it to her satisfaction.
Laying down the riding crop Mistress continued to slowly encircle Darrell
letting the back of her gloved hand gently stroke his panties.
Occasionally he could feel the knob of the dildo brush against his
pantied buns and rub back and forth against his sanitary pad. Mistress
was obviously enjoying it as much as Darrell and he parted his legs to
allow her dildo easier access to his crack.
Darrell's cock was at its hot throbbing hardest, pressing so hard against
his panties that the outline of his knob prominently displayed itself
through the silky material. Soon his panties would show the dampness of
his precum. He yearned for Mistress to fondle his cock and balls, and
then remove his panties so she could see Miss Dianella in her full
majestic glory. Instead Mistress continued to slowly encircle him,
brushing the back of her hand against his pantied buns and flanks,
anywhere but the one place Darrell yearned for her to touch. Darrell had
read about dominas and how they liked to tease their subs. Now he was
experiencing it for himself.
Finally, the agony was over. Mistress stood before Darrell and allowed
the knob of her dildo to gently rub against his throbbing hardness,
running it up the length of his shaft until their knobs kissed through
the silky panties. Darrell was ecstatic. Then with one hand Mistress
gently fondled his pantied hardness and knob as she fondled the dildo
with her other hand.
Mistress smiled sweetly and asked, "Like to fondle girlie cock would
you?"
Darrell reached out and took Mistress's dildo in his gloved hand. The
latex shaft felt soft and spongy to the touch. The sensations he felt
coursing through his body were far more erotic that the sensations he
experienced when feeling many sissyboy cocks. Mistress continued to
fondle Darrell's cock, alternately gently squeezing the length of the
shaft, then caressing his most sensitive knob through the panties.
Darrell felt Mistress's hand cupping his balls. He winced as Mistress
gently squeezed them.
"Like that, do we? You are such a naughty girl," Mistress said as she
continued to fondle Darrell's cock.
Darrell was so overcome by the erotic excitement of the experience that
he could only nod in reply.
Finally, Mistress decided it was time to put Darrell out of his misery.
Standing behind him she slipped her hands under the waistband of his
panties and gently eased them down. Darrell felt the silky material
passing over his buns and then Mistress guiding the panties over his
cock, letting them gently kiss his stockinged legs as they fell. Darrell
stepped out of the fallen panties. His cock was so hard, it seemed to
take on a life of its own.
Mistress stood back to admire the erotic vision that presented itself.
"Are we having our period then?" she said, noticing the sanitary pad
between Darrell's legs.
"Yes, Mistress. It's my time of the month. I hope it's all right with
you."
"Of course it is, you silly girl. You would be surprised how many of my
girlie sissyboys wear sanitary pads and tampons as part of their feminine
persona. I consider that it is an essential part of every sissyboy's
transition to femininity. And you, my dear, are obviously already well on
that journey."
Mistress picked up his discarded panties. Her gloved hand gently enfolded
Darrell's cock as she buried her face in their black silkiness, savouring
his sissyboy aromas they contained. Her eyes closed as she relished his
hardness, feeling it throbbing with his erotic excitement.
"Mmmmmmmmmmm," she purred and she fondled the hardness of his shaft. "You
wear such exquisite perfume. It's just so, so erotique."
Darrell was grateful that just before he left the office that day he had
slipped into the washroom and sprayed perfume into his panties. As Diana
he loved the warm effeminate feeling of the perfume on his cock and
balls.
As Mistress savoured the aroma of his perfumed panties, the dildo knob
ran back and forward along Darrell's shaft. She looked slyly at him as
once again, their knobs kissed and gently rubbed each other.
Her gloved hand resumed fondling Darrell's shaft.
"These are such lovely feminine panties. You must really be in love with
your cock."
"I am, Mistress."
"Yes. Most of my girlie sissyboys are. Some are really infatuated with
their cocks, so much so, they think about little else. Are you infatuated
with yours?"
"Actually, I consider her to be a young lady, Mistress."
Her hand tightened its grip on the shaft. "Interesting. Does this young
lady have a name?"
"I call her Miss Dianella, Mistress."
"Yes, how appropriate. How do you do Miss Dianella. I am Mistress Natasha
and I hope that when you leave you will be more than satisfied with
today's activities," she said as she gave his cock one last squeeze.
Mistress Natasha removed the scarf from Darrell's neck.
"Open your mouth please," she said, as she walked behind him.
Darrell immediately obeyed and he could feel the knob of the dildo
brushing against his buns as Mistress placed the scarf in his mouth,
wrapped the scarf around his head and tied it at the back. Darrell was
now securely gagged.
Mistress now took a fur lined leather cock strap and wound it round the
base of Darrell's cock just behind his balls. Darrell winced as Mistress
tightened the strap to its last notch.
"That will keep Miss Dianella hard for the remainder of the session."
Mistress picked up Darrell's discarded panties and draped them over her
dildo, and fondled her shaft. She then draped the panties over Darrell's
hardness and fondled his shaft and knob. It was most erotic for both of
them.
Having resumed fondling her shaft with the panties Mistress walked over
to a small side table. As she returned Darrell could see she was holding
a leather slave collar in her hand. Standing behind Darrell she placed
the collar round his neck and strapped it in place. The collar was fur
lined and although it forced Darrell to hold his head erect, it fitted
comfortably.
The collar had a chain leash hanging down the front. Mistress took the
leash in her hand and still fondling her dildo through Darrell's panties,
led him over to the chair on which the nightdress lay.
Darrell could hardly walk with the pain from the tightness of the cock
strap but he had no choice but to follow. Somehow he managed to cross
over to the chair.
"Now pick up the nightdress please," Mistress instructed
He lifted the nightdress from the chair and held it against his body,
savouring the most erotic touch of the cool silky smoothness against his
soft sensitive skin. He buried his face in the silk and sweetly kissed
the soft material before caressing his body with the silk. He then
wrapped part of nightdress round his throbbing hardness and fondled his
shaft and knob. The touch of the cool silk against his burning knob was
most blissfully erotic.
Mistress smiled as she watched Darrell pleasuring himself. Realising that
he was about to cum, she stepped in. "You must really have a strong
lingerie fetish as you seem to enjoy the erotic delights of soft silky
femininity, you lucky girl."
Being gagged, Darrell could only nod in reply.
"Now let's see what else you do to pleasure yourself, you naughty girl."
Standing with his legs apart, his throbbing cock showing its full
majestic glory Darrell held the nightdress in front of him so that its
soft silkiness just kissed the tip of his knob. He slowly lifted and
lowered the nightdress, so that it gently brushed against his knob. Soon
he could feel the cum rising in his shaft and he wrapped the skirt of the
nightdress round his throbbing hardness to catch the cum.
As she watched him Mistress Natasha continued to fondle her dildo through
Darrell's panties. "Better stop now as I have many more erotic delights
in store for you before you cum."
Once more Darrell buried his face in the perfumed soft silkiness as
Mistress led him to a small secluded alcove which opened off the main
room. Again he felt the excruciating pain from the cockstrap as he
walked, but now the sensation was becoming erotic.
Looking round the alcove Darrell saw that it contained a bed, a small
side table with several items placed on top, and a padded footstool.
"Spread the nightdress over the bed please."
Darrell quickly obeyed making sure that the nightdress was spread
perfectly flat.
"Now lie on top of it and spread out your arms and legs."
Darrell lay down on top of the nightdress, his head resting on a soft
scented pillow. The coolness of the soft silk against his smooth,
sensitive skin was heavenly. He spread out his arms and legs. Gazing
upwards he saw that a mirror covered the entire ceiling of the alcove. He
could now observe every move Mistress Natasha made, and at the same time
admire his own erotic beauty.
He watched in the mirror as Mistress picked up four fur-lined cuffs each
of which was attached by a chain to a corner of the bed. She inserted
each wrist in a cuff and then repeated the process for his ankles,
tightening the chains so he was spread immobile on the bed. Satisfied
that the chains were drawn tight enough, she removed the leash from the
slave collar and attached the collar to a clip which lay under the
pillow.
Bending down, Mistress picked up the end of a leather strap and threw it
across the bed. She walked round to the other side of the bed and
inserted the end into a buckle and drew it tight. Charles was now
completely immobile. His wrists and ankles restrained by the cuffs and
the strap tight across his chest held him to the bed.
Gazing up at the mirror the narcissist in Darrell saw himself lying
spreadeagled on the bed unable to move. His burning cock throbbed with
erotic anticipation. As he gazed at his reflection, he was lost in the
wondrous rapture of his own beauty, his angelic face framed by the
shoulder length girlie hairstyle he favoured. His black lingerie
contrasted against his smooth sensitive milky white skin. He was really
such a beautiful young man and it was no wonder that other sissyboys
loved to play their erotic games with him. Darrell had very little body
hair, mainly around the base of his cock and trailing back between his
legs to his little pink rosebud. A weekly application of a depilatory
cream down there kept his skin smooth and sensitive to rub against his
silky lingerie.
As his eyes drank in his own beauty his mind wandered back a few nights
to when he met two most beautiful young prettyboys in one of the gay
saunas he frequented. As he kissed and fondled one young man, he felt the
other take Miss Dianella in his mouth to give her the most wonderful blow
job. Darrell and Diana preferred to fondle and masturbate Miss Dianella,
but this young man's technique was so wonderfully erotic, and as he
sucked Miss Dianella the young man masturbated his own cock. While all
this was happening between his legs Darrell was caressing and fondling
the other young man, their tongues eagerly exploring the far corners of
each other's mouth. Eventually all three climaxed together, in a orgy of
homo-ecstatic blissfulness.
None of the three had ever met before, and given the transitory nature of
the gay milieu, it was unlikely they would ever meet again. As Darrell
lay savouring the erotic memory of the encounter, he relaxed and drifted
into Diana, allowing her to take over.
"Are you quite comfortable, my dear?" Mistress asked. "If you want freed
at any time just wiggle your feet."
Darrell could only manage a brief nod.
Removing his panties from her dildo she buried her face in them savouring
their perfume once more before draping them over Darrell's face, and then
lifting them with her riding crop she let the panties drift along his
body, their soft silkiness kissing his most sensitive skin. When she
reached his throbbing hardness she allowed the panties to kiss his knob
and then ran them gently up and down his shaft and ball sac, allowing
them to gently brush against the smoothness of his skin. Again, the
erotic sensations were heavenly.
Mistress then draped the panties over Darrell's cock, gently fondling his
shaft and knob through the silkiness. His cock throbbed with excitement.
His immobility caused by the restraints of the cock strap and cuffs only
heightened the erotic sensations.
Mistress picked up a latex vagina from the side table.
"I suppose being inside a vagina will be a new experience for Miss
Dianella."
She placed the vagina over Darrell's silken encased hardness, firmly
pressing it down until it took the whole length of his shaft. Having his
cock encased in a vagina, even an artificial one, was indeed a new
experience for Darrell. He much preferred to take the passive role in a
relationship, allowing his orifice of love to welcome the other
sissyboy's cock and enjoying the thrusts of the cock inside him until he
could feel the cum rising up the throbbing shaft, and then the erotic
sensations of the hot sticky mass bursting inside him flooding his
sissyboy pussyhole.
Except that when he was at a gay party and the sissyboys decided to form
a daisy chain, Darrell would play his full role, taking one sissyboy's
throbbing cock up his orifice of love, with his own throbbing cock inside
the little pink rosebud of the sissyboy in front. And then the erotic
vibrations coursing through the circle as each sissyboy's pussyhole
received the cum from the sissyboy behind him, which caused him to shoot
his own cum into the sissyboy in front.
With her gloved hand Mistress gently stroked Darrell's ball sac, then
moved his sanitary pad aside and gently prodded his little pink rosebud.
She appeared to be satisfied at what she saw.
Walking over to the table she returned with a tube of lubricant. With one
finger she moistened Darrell's rosebud, gently inserting her gloved
finger inside to ensure that he was well lubricated. For Darrell, the
sensation of Mistress's finger wiggling inside him was delightfully
erotic. A thought flashed through Darrell's mind. Was Mistress going to
mount him and service his sissyboy pussyhole with her dildo? Darrell had
taken sissyboy cock up inside him many times and had often fantasised
about what it would be like to feel a dildo instead. Was he now about to
find out?
Satisfied that Darrell's rosebud was well lubricated, Mistress returned
to the side table and picked up the most realistic veined dildo.
"It's similar to the one I'm wearing, my dear. I like my girlie sissyboys
to share my erotic pleasures," Mistress explained as she lubricated the
shaft. Darrell tensed as he felt the knob of the dildo entering his
rosebud. Mistress was gentleness itself. Once the knob had passed the
entrance of his rosebud Mistress stopped to allow Darrell to relax. This
was always a difficult point for Darrell as he was rather tight down
there, even though he had been penetrated many times by sissyboy cocks.
Darrell relaxed his sissyboy vagina muscles, and he felt the latex dildo
slowly slide up inside him until he had accepted its full length. Darrell
tensed and relaxed his muscles to welcome the dildo into his orifice of
love. It felt warm and spongy inside him, not at all like many of the
sissyboy cocks he was used to. This was truly a new experience.
With the dildo firmly in place Mistress replaced the sanitary pad over
its base.
"That will stop it slipping out. You'd be surprised at how many sissyboys
can't keep girlie cock inside them once we get started."
Darrell watched in the mirror as Mistress attached wires from the vagina
and the dildo to a small generator which stood on the table.
"I'll start very gently and then speed things up. OK? Remember If you
want to stop just wiggle your feet."
Darrell nodded.
Soon Darrell could feel a strange throbbing rhythm pulsating through his
body. It seemed to emanate from his cock and deep inside his sissyboy
vagina. Mistress pulled up the padded footstool, and placing one foot on
the stool, gently fondled her dildo as she watched Darrell. She
occasionally adjusted a knob on the generator and Darrell could feel the
vibrations becoming more intense.
For what seemed an age she teased Darrell with the intensity of the
vibrations. Sometimes it would be the vagina which vibrated the most with
the dildo quietly throbbing away inside him. Just as Darrell thought he
was going to climax, she would increase the intensity of the dildo's
vibrations, and reduce those of the vagina.
As Mistress watched his erotic pleasure she slowly started to rub her
dildo. Unknown to Darrell the harness held another dildo inside her
vagina and a butt plug up her ass, so she could savour both vaginal and
anal delights. As Mistress increased the frequency of her strokes she
intensified both the vaginal and dildo vibrations coursing through
Darrell. For Darrell this was the agony and the ecstasy. He dearly wanted
to climax and relieve the pressure in his cock and balls, but at the same
time he yearned for the experience to last forever.
At last Mistress gave an involuntary shudder as she climaxed, and in the
mirror Darrell watched himself jerking in erotic ecstasy as his cum laden
balls shot spurt after spurt of hot sticky cream into his panties.
Mistress adjusted the generator until the vibrations through the vagina
and dildo were reduced to a soft throbbing pulse. She picked up a small
notebook and leafed through it as Darrell lay slowly recovering from his
experience.
"Yes, I think Mistress Tanya will be the ideal choice to assist in your
fantasy. She is always on the lookout for something new to try and this
will be right up her street. I'll give her a call and contact you once we
have arranged a suitable time."
Although Mistress had switched off the generator, Darrell could still
sense the vibrations pulsating through his body. His knob felt the hot
sticky cum on his panties. Mistress removed the vagina from his cock and
slid the dildo from his sissyboy vagina; before releasing his cuffs and
removing the cock strap.
Returning to the room where they first met, Darrell went behind the
screen and resumed his male persona. As he was about to leave Mistress's
lips gently brushed his cheek.
"I hope you enjoyed today's experience," she whispered in his ear. "And
what lovely panties you wear. Diana must really love you to choose such
exquisite lingerie. I'm sure that Mistress Tanya will agree with me when
you both meet to fulfil your fantasy."
At this, Darrell's sissyboy vagina muscles tightened on his sanitary pad.
Inside him Diana was swelling with pride and to his erotic delight,
between his legs he could feel Miss Dianella recovering her hardness. He
had taken the first step to live out his most secret fantasy, now he had
to wait Mistress Natasha's pleasure.
Chapter 2
An Erotic Tryst Is Arranged
It was one morning several weeks later when Darrell woke with a feeling
that something wondrous was going to happen that day. Not that there was
anything out of the ordinary in his daily morning routine.
As usual Miss Dianella was up well before him and as Darrell lay fondling
the young lady's hardness through a pair of soft silky panties, his mind
wandered back to the delightfully erotic pleasures he had experienced the
previous weekend at an orgiastic party given by one of his sissyboy
friends. As with many sissyboys on these occasions, Darrell's orifice of
love had been the recipient of many cocks and he savoured the erotic
pleasures of feeling hot throbbing cock after hot throbbing cock
thrusting inside him as the sissyboys queued up to ravish him, and then
the erotic rapture of their hot cum bursting forth deep down inside.
And what marvellous erections they had. As one sissyboy was thrusting
inside him Darrell was frequently engaged in mutual fondling and
masturbating another sissyboy. At the end of the party his cock was dry
after spilling so much cum.
Now he was paying for these pleasures. As he lay fondling his hardness he
could still feel some discomfort down there even though he had a
maternity size sanitary pad pushed up inside his sissyboy vagina.
Although it was not Diana's time of the month she had insisted that to
ease his discomfort, Darrell wear one of the thick maternity size
sanitary pads that she used during the heaviest days of her menstrual
period. Diana was such a demanding lady and Darrell could do no other
than to obey her, and after all it was as much for her comfort as it was
for his own.
Both Darrell and Diana preferred to sleep enveloped in the erotic
pleasure of soft silk pyjamas. Over the years they had experimented with
many girlie outfits as sleepwear - full length silk nightdresses, bra and
silk panties, silky babydoll pyjamas, ballerina length half slips and bra
- but in the end they both agreed that lady's silk pyjamas and a matching
bra were the most erotic of the garments they had worn. Pyjamas allowed
Darrell and Diana to easily slip their hand under the waistband and play
with Miss Dianella whenever they wished.
Last night Diana had chosen a pair of red pyjamas and a matching red bra
for Darrell to wear. The tightness of the bra around his chest enhanced
his feeling of girlieness. Because Darrell was a compulsive masturbator
Diana insisted that he wrap a pair of panties round his cock to catch his
cum and prevent it staining his pyjamas. As Darrell had spent much of the
night hours fondling Miss Dianella and masturbating, the dried cum stuck
his panties to his knob. He winced at the erotic pain he felt as he
gently removed his panties from his knob.
Once more Miss Dianella was hard. Darrell reached across to the other
pillow where Diana had thoughtfully left another pair of red panties.
Draping the panties across his face, Darrell kissed the soft silky
material as he once more rubbed Miss Dianella. As the cum rose up his
shaft his silk encased body slid against the black satin sheets Diana had
chosen, and he writhed in the rising orgasmic bliss as he felt the hot
juice bursting into his panties. Reluctantly, he realised it was time to
get up.
The sensation that something important was going to happen today hung
around as Darrell rose and had a long hot shower. Still wearing Diana's
sanitary pad he bent over to allow the hot water to soak into the pad
until he could feel it swelling inside him. Ah, what erotic comfort the
sensation brought. Even Diana enjoyed it as the wet pad helped to eased
the discomfort in her pussyhole. With one hand he pressed the swollen pad
up into his orifice of love and felt the hot water entering up inside
him. With his other hand he wrapped his wet panties round his cock and
masturbated one last time, relishing the layers of soft silkiness rubbing
against each other until he felt the hot cum rising through his shaft and
bursting into his panties, before patting himself dry with a warm fluffy
towel.
Standing naked in his dressing room, admiring his beautiful slim body in
a cheval mirror, he sprayed a vaginal deodorant into his most intimate
parts. Crouching down he spread his sissyboy vagina cheeks with one hand
while with the other he sprayed the deodorant up his pink rosebud and
into his orifice of love, before spraying his balls and along the
underside of his throbbing shaft. The erotic touch of the cool scented
air of the deodorant against his most sensitive skin was divine. Resuming
his stance he sprayed his along the upper side of his shaft and then his
knob.
Satisfied with the sweet aromas arising from his most intimate girlie
bits, he inserted another of Diana's maternity size sanitary pads into a
sanitary vee belt and sprayed the deodorant along the pad. Darrell fitted
the vee of the belt under the base of his cock and folded back the front
tab to form a cushion, before crouching down and pushing the pad deep
into his orifice of love. The act of fitting his cock through the vee and
the sensation of the fresh scented pad inside him always made him feel
most girlie.
Now came the erotic garments Diana had selected for him to wear that day.
This morning it was midnight blue lingerie with black stockings. Standing
before the mirror, Darrell arched his back as he hooked his bra. Once
more Miss Dianella stood proudly erect, and bending backwards only
further enhanced the full majestic glory of her hardness. He then donned
the garter belt admiring his rigid cock as he hooked it up.
And then came the sheer black stockings. As Darrell gazed at himself in
the mirror he let the wispy stockings gently kiss his knob, before
sliding them up over his smooth legs and fastening the garters. As he
rolled the stockings up his legs his wrists touched his hot knob. Gazing
at his reflected loveliness in the mirror he savoured the erotic
sensation of the soft silkiness enveloping his legs pulling the garter
belt tightly down on his hips.
Still admiring his reflected beauty Darrell placed one foot on a small
cushioned stool and gently ran his hands up his stockinged leg to smooth
out any wrinkles. As his hands came close to his throbbing hardness he
could once more feel the heat radiating from his knob. He then turned his
attentions to the other leg and after ensuring his stockings were
completely smooth, he allowed his burning knob to kiss the wispy nylon.
Ah, what sheer erotic blissfulness.
Then came his most wonderful silky directoire knickers. For Darrell these
were the most erotic garments in his collection filled with erotic girlie
clothes. Picking up the directoire knickers he gently buried his face in
their soft silkiness before draping them over his throbbing hardness.
Gazing in erotic ecstasy at his reflection, Darrell gently fondled his
throbbing cock through the layers of silkiness, paying particular
attention to massaging his knob with the soft material. Ah what erotic
bliss he experienced as he felt the silky layers sliding over each other.
Directoire knickers held particular erotic memories for Darrell. Ever
since he could remember he had worn Mummy's silky knickers - nights,
weekends and holidays, as they satisfied his desire to be the girl he so
wanted to be. Each Monday he would rush home to see what knickers Mummy
had chosen for him to wear that week. Then one day, just past his
nineteenth birthday, he had returned home to find a pair of Mummy's
powder blue silky knickers lying on his bed. He had just been advised of
the success of his university application and as a special treat Mummy
was letting him wear a pair of her best knickers.
Stripping off his male clothes he had stood naked, his face buried in the
cool silk of the knickers. He had just donned the knickers, when he
experienced a new sensation between his legs. Gazing in the mirror he saw
his cock had become hard and was tenting the knickers. Very gently he
fondled his cock and knob through the silk. Ah what erotic bliss he
experienced.
This was how he experienced his first erection, and oh how erotic that
experience was. He had stood for what seemed like hours wearing only
Mummy's knickers, gazing at his reflection as he fondled his shaft and
knob through their silkiness. After a while he felt his cock shrinking in
his knickers, and although he wore them for the rest of the day and slept
in them that night, the hardness did not return.
The next day as he bounded up the stairs he felt his cock harden in
anticipation of the erotic delights which awaited him. He was not
disappointed. The erotic sensations he had when wearing the knickers were
even more delightful than the previous day and over the next few days he
discovered that just thinking about those most erotic garments was enough
to harden his cock.
The local sports day was being held on the Friday and as his attendance
was not compulsory, Darrell could wear Mummy's knickers from Thursday
afternoon through to Monday morning. Lying in bed on the Thursday night,
Darrell lovingly fondled his new found hardness and his knob through
Mummy's knickers. And for some unknown reason he oh so gently rubbed the
loose skin of his shaft. The pleasure was most erotic and soon he felt
something rising through his shaft. Although he was terrified he was
going to wet himself, he could not stop rubbing, and as the cum rose in
his shaft he rubbed ever harder, until he felt the cum explode into his
knickers. As his cock quickly softened he immediately felt a sense of
erotic relief. Thus did Darrell have his first masturbatory experience.
Darrell remembered how that night, he had felt the hot sticky cum through
the knickers and was too frightened to look in case it was blood. Only
the next morning did he pluck up the courage to look into the knickers
and saw the white crustiness of the dried cum. Night after night he lay
in Mummy's knickers with the legs rolled up as far as they would go,
playing with his hardness through the silky material and then
masturbating with their silkiness wrapped round his shaft.
At first Darrell only masturbated once each night before falling asleep,
but after a short time he had no sooner experienced one orgasm, when he
was fondling his cock through his knickers into a new hardness for
another masturbatory session. Soon he was masturbating several times each
night before going to sleep and again in the morning before getting up.
Often he would wake up during the night only to fondle his cock into a
new hardness and masturbate, sometimes his cock was already hard when he
awoke.
It was a few weeks after that first experience that Darrell had the
courage to actually watch himself masturbate in daylight. It was the
summer and he could wear Mummy's knickers 24/7. Mummy had gone out for
the afternoon and he had been leafing through some ladies' magazines. As
he gazed at the pictures of the girls he fantasised about what it would
like to wear their clothes. Soon his cock was at its throbbing hardest in
Mummy's silky knickers.
Unable to resist the temptation any longer, Darrell rushed upstairs to
his room and quickly stripped off his male attire. Clad only in Mummy's
knickers he gazed at his reflection as he fondled his shaft and knob
through their soft silkiness. He opened the waistband of the knickers and
admired his hardness tenting the knickers, before inserting his hand
inside and gently fondling his shaft. Removing his hand he resumed
fondling his shaft and knob through the silky material and saw the first
damp marks of the precum where his knob pressed against the knickers. It
was time to start rubbing.
Still admiring his reflection, he pulled the knicker legs up to his
crotch and, gathering the loose material round his shaft, he started to
masturbate, initially with long slow strokes that pulled the skin the
length of his shaft, and then as the erotic excitement grew, quick short
strokes concentrating just behind his knob. As he rubbed he could feel
the erotic touch of the loose material of the knickers brushing against
his balls. And then, as he felt the cum rising in his shaft, his strokes
gradually slowed until his body jerked as the spasms of cum wet the
knickers.
All this while he had been watching himself in the mirror. As he felt his
cock slowly shrinking, he opened the waistband of the knickers to see his
knob covered in a white sticky mess. Taking some of the cum on his finger
he rubbed it against his chest until his skin had absorbed it. He quickly
fondled his cock into another erection and once more he watched himself
in the mirror as he masturbated into the knickers, before resuming his
male attire and returning to the ladies' magazines to fantasise over the
pictures.
Since that erotic experience hardly a day had passed when Darrell had not
masturbated at every opportunity and over the years he had experimented
with various masturbatory techniques involving various items of lingerie
in an endless search for ever more erotic delights. Sometimes he
masturbated so much that he broke the skin on the underside of his cock,
just below his knob, and the dried blood stuck his cock to his panties.
Oh the pain he felt on these occasions when he had to remove his panties
from his cock.
Darrell had always been aware of his feminine persona, lying in bed each
night wishing that his life so far had only been a dream and that when he
awoke he would really be a girl. Unfortunately, each morning brought
disappointment, but with his sexual awakening his love of lady's clothes
took on a new significance. No longer was it just dressing up in Mummy's
clothes to feel girlie. Now dressing up in these clothes took on a whole
new meaning. The erotic sensations that came from wearing female
clothing, particularly soft silky lingerie, made him feel that he was
actually being transformed into a girl. It was at this time that Diana
had at last emerged to take her rightful place as his female persona,
into which Darrell could retreat whenever he could.
Not that Darrell accomplished this transformation into Diana on his own.
Mummy had played a large part in Diana's blossoming into the beautiful
lady of Darrell's dreams. Recognising the erotic pleasures Darrell got
from wearing feminine finery and his desire to be girlie, Mummy welcomed
his female persona of Diana into the family.
For years Darrell had watched Mummy as she dressed, mimicking her actions
as he secretly dressed up in her clothes. Now, Mummy carefully observed
as he dressed up as Diana, advising him on make up, how to colour
coordinate his clothes and how to style his hair. For hours she had him
practice walking around the house wearing a tight skirt and balancing on
high heels. She showed him how to smooth his skirt when he sat down to
avoid creasing it and how to discretely cross his legs without flashing
his panties.
As Diana blossomed into womanhood, Mummy introduced Darrell into the
mysteries of the female menstrual cycle. Darrell had already started to
experience certain times in the month when he was masturbating almost
continually and had an uncontrollable urge to shop for girlie clothes,
particularly lingerie. On discussing it with Mummy, she told him that as
Diana he had started to have sissyboy menstrual periods. Mummy had taught
him how to work out when his period was due, how to use sanitary pads
during his heaviest days, how to insert tampons into his little pink
rosebud, and the erotic delights of spraying a cool scented vagina
deodorant up into his orifice of love and along his throbbing shaft.
His slender body and feminine features allowed Darrell to easily pass as
a girl or boy, and with Mummy's help he styled his hair to further
enhance his feminine looks. After much practice in the privacy of their
home, Darrell could finally dress as Diana and accompany Mummy as her
daughter when shopping for his girlie clothes, usually during his periods
when he felt most girlie. He could even use the ladies rest rooms in the
department stores they patronised. For Darrell all this was a dream come
true, he felt that he really was a girl even though he usually had a
throbbing erection between his legs.
The arrival of unisex clothing on the fashion scene brought Darrell more
erotic pleasure. He quickly accumulated a wide range of ladies outerwear
- pant suits, silky business shirts, flat lace up shoes. As Diana he
could dress completely in ladies' clothes to satisfy his craving for
femininity, while still presenting himself to the outside world in his
male persona as Darrell. It eventually reached the stage where the only
items of male clothing in his wardrobe were the three piece suits which
were de rigueur for budding senior executives at his office. The rest of
his extensive wardrobe belonged to Diana.
It was Diana who thought about calling his cock Miss Dianella. As a cock
she provided both of them with such wonderful erotic pleasures and Diana
suggested that she join then with a personality of her own. The young
lady required her own name and so she became Miss Dianella, taking her
rightful place as one of the family. And now he had reached the stage
where he spent more time Diana than he did as Darrell.
All this while as he mused, Darrell had been fondling his shaft and knob
through the gorgeous silken loveliness of knickers, savouring the erotic
pleasure of the numerous layers of soft material rubbing over each other.
Sadly, he realised that Diana had at last to give way to Darrell. He
stepped into the silken garments feeling the soft erotic kiss of the
silky material against his stockinged legs as he drew them up. For
Darrell this was the most erotic moment of his dressing. Bending down to
arrange the elasticised knicker legs he saw in the mirror his throbbing
hardness tenting his knickers and the small damp spot caused by his
precum.
Gazing at his reflected beauty, he lovingly fondled his shaft and knob
through the silkiness. Realising the time, he opened the waistband and
sprayed perfume into the knickers. His cock and balls luxuriated in the
erotic warmth of the perfume as he arranged his hardness so it hung down
one leg. Both Darrell and Diana liked Miss Dianella to luxuriate
comfortably in her silken cocoon all day and Miss Dianella's hardness
showed her erotic delight as his knob pressed against the knickers.
Back in his male persona Darrell donned his ladies' white silk shirt and
then his male 3 piece suit, topping of his ensemble with flat slip-on
shoes, ladies' shoes of course. As he left his apartment he hoped that
today, like most days, would provide many opportunities for him to drift
into Diana for a few brief erotic moments.
As Darrell journeyed to the office the sensation that something important
was to happen that day further intensified. Even travelling to the office
each day was erotic bliss and this morning was no exception. Darrell
considered that the central business district of any city during the week
was the best free fashion parade there could be, and that morning the
young ladies seemed to have put on a special show just for him. Those
tight black pencil skirts highlighting the girls' rounded derrieres,
their long slender legs encased in black nylon with feet shod in stiletto
heels, and short tight jackets emphasising their waists, to Darrell it
was all so, so erotique.
Darrell's fetish for feminine finery was so intense that when he saw a
well dressed young lady he had an overwhelming desire to wear her
clothes. He loved to fantasise whether the girls were wearing pantihose
or stockings, and if stockings were they stay ups or held in place with a
garter belt; was she wearing a slip, and what panties, if any, was she
wearing and were they as pretty and as feminine as the panties he was
wearing at the time, and was her lingerie colour coordinated as Mummy
always insisted for his?
The sight of those beautifully clad ladies and the erotic fantasies they
engendered in Darrell, always brought Miss Dianella to a such a state of
erotic excitement in his knickers so that her hardness forced his knob to
rub against the silky material as he walked. And this morning was no
exception. Before he had even reached the safety of his office Darrell
had creamed his knickers several times.
After panties and knickers, slips were the most essential garment of
Darrell's fetish for feminine finery. More than once that morning he
caught a glimpse of the scalloped lacy trim of a slip and he fantasised
whether the girl was wearing a full slip or a half slip, which only
further heightened Miss Dianella's erotic excitement.
Diana always insisted that Darrell wear a full slip when dressed in his
girlie clothes. Mummy had taught her that a lady wasn't properly dressed
unless she was wearing a full slip. Not that Darrell minded at all, as
wearing a slip was a most important part of his transition into his
female persona. As Diana he would stand in front of the mirror dressed in
bra, garter belt, stockings, panties and heels with a thick sanitary pad
pushed into his orifice of love, what little make up his girlie face
required, and his hair arranged in the latest fashion. Yet what stared
back at him from the mirror was a sissyboy indulging his passion for
dressing up in girlie clothes.
It was only when he donned a slip that he was completely transformed into
his feminine persona, and Diana finally emerged in her full glory. This
was what he termed his defining moment as the lady of his dreams smiled
back at him from the mirror. Such was the intensity of Darrell's mutation
into Diana that she could then don a blouse and skirt and spend all day
without once touching herself down there. Diana would browse through her
collection of lingerie catalogues selecting garments for Darrell or
indulge in her favourite lesbian erotica, and yet Miss Dianella could
rest undisturbed cocooned in her silkiness.
As she accompanied Darrell that morning, Diana, ever the fashionista,
made mental notes of the girlie clothes that most excited him and pleased
Miss Dianella. She would seek out similar garments the next time she took
Darrell shopping. Darrell's cock throbbed so much in anticipation as he
fantasised about shopping for these clothes and then wearing them, that
he creamed his knickers once more.
It was halfway through the morning when the phone rang. Had the long
awaited call for which he had been hoping and dreading finally come? With
the erotic excitement of the morning, Miss Dianella had been at her hot
throbbing hardness between his legs. Sitting behind his desk Darrell had
spent all morning fondling the young lady as he fantasised about the well
dressed young ladies he had seen that morning and what it would be like
to wear their clothes. His knickers were now wet and sticky with his cum.
"Is Diana dressed today?" the voice asked.
Immediately recognising Mistress Natasha's soft, sultry tones Darrell was
filled with erotic excitement and could only answer "Yes, Mistress."
"Can I speak to her then, please," the voice continued.
"I'll get her for you straight away, Mistress."
As Darrell walked over to the office door he could feel his knob rubbing
against the silkiness of his knickers and he hoped that in his excitement
he wouldn't cream them again. Not just yet.
He looked into the corridor to see if anyone had overheard him. Satisfied
that no one was around, he closed the door and resumed his seat. The
erotic pleasure of his knob rubbing against the silkiness as he walked,
was electrifying.
"Diana here, Mistress."
"Darrell tells me you are dressed. Like to tell me what you're wearing
today?"
"All midnight blue today, Mistress. Matching bra, garter belt, silky
directoire knickers and black nylons."
"Mmmmmmmmmmmm," Mistress Natasha purred. "Any protection?"
"Yes, Mistress, I've got a maternity size sanitary pad pushed up into my
pussyhole."
"Mmmmmmmmmmmmmm," she purred again
"At the weekend Darrell was very generous with his sexual favours at a
sissyboy party and now we are both suffering for it."
As he spoke Darrell tensed his sissyboy vagina muscles round the pad. The
girlie sensation was just so, so, erotique.
"Mmmmmmmmmmmmmm."
"Darrell had to take one hot throbbing cock after another up his
pussyhole. No sooner had one sissyboy shot his cum and withdrew than
another was ready to take his place.. At the end of the evening Darrell
had taken so much cum that I felt like a walking sperm bank."
"Mmmmmmmmmmmmmm," purred Mistress Natasha once again.
"Some sissyboys were somewhat rough in their thrusting's. I much
preferred your dildo up my pussyhole. It was gentleness itself the way
you serviced my pussyhole."
"Mmmmmmmmmmmmmm."
"Indeed Mistress. Darrell was so popular that many sissyboys quickly
regained their erection and came back for more. I'm amazed at how much
cum a young man's balls can hold."
"Mmmmmmmmmmmmmm."
"They were the most beautiful, slim young men, lovely smooth silky skin,
and what exquisite erections. And their stamina. I thought that they must
have been exhausted by all the action, but they must be well used to it
attending so many orgies as they do. I'm so sore down there that I've
made Darrell wear one of my thickest pads for my own comfort as much as
his."
"Mmmmmmmmmmmmmm. Tell me more."
Mistress Natasha was obviously enjoying this, Darrell thought, and
wondered if she was masturbating as he spoke.
"And it was not only my pussyhole that attracted them. Darrell's cock was
also in much demand. One after another they masturbated Darrell. Some
gave him a blow job while another sissyboy was thrusting up inside me.
And he couldn't keep his hands off other sissyboys cocks either. All in
all we both had the most marvellous erotic time. Only now we are paying
for it with the uncomfortable feeling in my pussyhole."
"Mmmmmmmmmmmmmm."
"Yes. Darrell usually has plenty of cum in his balls, but this time he
was masturbated until he was dry. And even then they didn't stop. The
next morning his panties had bloodstains where the exertions had broken
the skin of his shaft."
"Mmmmmmmmmmmmmmmm," Miss Natasha purred again.
Darrell thought she must really be enjoying this. He wondered if she was
masturbating as they spoke.
"Quite a few sissyboys were so much excited by Darrell's smooth silky
skin that they rubbed their knobs along his back for erotic pleasure.
Some even masturbated as they caressed Darrell's silky skin and let their
hot cum drop on his back. Then they rubbed the cum into his skin until it
was dry. Ah what erotic bliss that was."
"Mmmmmmmm. And Miss Dianella, is she hard today?"
"Off course Mistress."
"Would you like to fondle her for me?"
"I've been doing it all morning but I'll do it again just for you,
Mistress."
"Good girl. Darrell will be most proud of you."
For a few minutes Darrell fondled his throbbing shaft and knob through
the soft silkiness of his knickers. Suddenly he gave an involuntary gasp
as he felt the heat of the hot cum through his stockinged thigh.
"Creamed our knickers, have we, you naughty girl?"
"Yes Mistress. Are you annoyed?"
"Off course not. I like my girlie sissyboys to enjoy their pleasures,
just as I enjoy mine. I was playing with my cock as we speak, and we
actually came together."
Once more Darrell's hand returned to fondle his rapidly developing
hardness through his knickers.
"Now to business," Mistress continued. "I've spoken to Mistress Tanya and
she is most excited with your fantasy. You'll like Mistress Tanya, she
specialises in humiliation and forced feminisation of sissyboys like
yourself."
"You know Mistress, with my fetish for feminine loveliness I can never
understand why anyone has to be forced to wear ladies' apparel,
especially their lingerie. I just can't get enough of it."
"Yes, I understand Diana, but deep down most sissyboys actually love
being feminised. For many of them dressing up in girlie clothes is a very
private thing, and they find it most erotic to dress up and share their
secret pleasures with a real girl. Most sissyboys are exhibitionists and
dressing up in their female finery for a domina is one of their few
opportunities to show off."
"You think so Mistress?"
"Yes. And putting up a show of resistance, however feigned, adds that
special frisson of erotic excitement to the occasion," Mistress Natasha
replied. "They secretly love being dominated by a strong woman as it
makes them feel so girlie and vulnerable."
"I suppose your years of experience dominating sissyboys like myself have
given you an insight into our psyche, Mistress."
"Yes, I suppose it has. Now back to your fantasy, Diana. Mistress Tanya
should be at the height of her menstrual cycle in about ten days, so
would next weekend suit you? I suggest Saturday as that will give you
Sunday to recover."
"Saturday week will be great by me, Mistress."
"Good girl. Now here's what I want you to do in preparation."
Darrell quickly wrote down Mistress's instructions and placed the note
securely in his wallet. Until he got home that night the wallet would not
leave his person.
After Mistress had rang off, Darrell once more fondled his hardness until
he felt the hot sticky cum. As he had creamed his knickers so often that
morning and no doubt would cream them many more times during the day,
Diana would insist that they be washed and ironed before he could wear
them again.
Darrell made a mental note that when he got home that night he would have
a long hot scented bath in which he would wash his stockings and
knickers. He would insert his cock into both stockings so that the toes
kissed his knob. Over the stockings he would wear his knickers, the legs
pulled up to his crotch. Thus dressed, he would lie in the hot scented
bath fondling and masturbating Miss Dianella though the layers of black
nylon and silky knickers.
As he masturbated, he would feel the sanitary pad swell up inside his
sissyboy pussyhole as it absorbed the bathwater. He would let the water
soak into his sanitary pad, luxuriating in the erotic delight of feeling
the pad swell up between his buns. He would press the pad through his
knickers and feel the water entering his pussyhole, and then let the pad
swell up once more.
Better still, for added erotic pleasure he would let Diana take charge of
the proceedings. He just loved the way she fondled Miss Dianella, and
then those long slow strokes with which she rubbed the skin up and down
the whole length of his shaft. encased in its silken loveliness, the
experience would be even more erotique. At that thought he could feel the
first stirrings of a yet another hardness developing down there.
Chapter 3
Dreams Really Do Come True
After an agonising ten days Darrell once again stood at Mistress's door
ringing the bell. Again the door was opened by a remote unseen hand and
Darrell stepped into the hallway. In his hand he carried a small parcel,
as he had been instructed. The parcel was still sealed as it had been
since he left the shop.
This time Mistress Natasha was waiting for him in the hallway. She wore
only a pair of full brief style panties in a midnight blue shade.
"Pleasure to see you again, Darrell," she said as she gave his cheek a
welcoming peck. "We'll use this room today."
Taking his parcel she led him into a room halfway down the corridor. The
room had one other occupant, a tall slender girl dressed in bright red
panties of a similar style to those worn by Mistress Natasha.
"This is Mistress Tanya, Darrell. She is as excited as I am about what we
are all about to experience. Now are you dressed as we discussed."
"Yes, Mistress Natasha."
"Very good. Now go behind that screen and transform yourself into Diana."
Once behind the screen Darrell quickly removed all his male attire. As he
stripped off, he fantasised about Mistress Tanya. She was most beautiful
with her slim boyish figure, lovely long legs, and her angelic face
topped by her blond hair done up in a ponytail. "Oh those legs", he
mused, "they must look wonderful in black stockings and heels". And that
slim boyish figure. How wonderful if she only had a cock between her
legs, she would be such delight to fondle.
"Are you ready now?" Mistress Natasha asked.
"Yes, Mistress."
"Then emerge as Diana for the erotic pleasure of Mistress Tanya."
Slowly, Darrell came round the screen. He was clad in only a pair of
flame coloured silky directoire knickers. The hardness of his cock
tenting his knickers displayed the state of his erotic excitement.
"What lovely, lovely knickers," cooed Mistress Tanya. "And what a
wonderful cock inside them. You must really be very excited."
"That's Miss Dianella I was telling you about," explained Mistress
Natasha. "Come Miss Dianella I'd like you to meet Mistress Tanya."
Mistress Tanya gently took hold of Darrell's knickered cock and fondled
it through the soft silk. Her touch was softness itself. Starting by
fondling his ball sac, her hand worked its way along the shaft until it
reached his knob. As she fondled his silken encased knob Darrell felt a
stabbing pain shoot up the centre of his cock, ending somewhere deep
inside him. It was as if someone had pushed a needle into his cock. It
was just oh so, so erotique.
"Are these your favourite style of knickers?" Mistress Tanya asked.
"Yes, Mistress. They hold much erotic affection for me. I had my first
erection while I was wearing Mummy's knickers, and then a few nights
later I had my first ma